Episode #356 – The Secret to Making Your Next Vacation the Best Ever

Today, we’re discussing the secret—my secret—to making your next vacation the very best ever.

Hello! If you listened to the last episode of this show, you know that I recently returned from our family vacation. We spent two weeks traveling to five cities in three countries on two continents. It was a big trip! If you missed episode 355, I recommend going back and listening to that one if you want some context on the trip itself. We visited Spain, Portugal, and Morocco on this journey, marking our first significant trip in five years. In that episode, I discussed the principles that made our trip meaningful, successful, and memorable. There was also another topic I wanted to delve into, but I ran out of time, so this episode is essentially part two of that discussion.

Today, I want to share a remarkable insight about what truly made this vacation extraordinary. It all comes down to one word: expertise. By actively sourcing experts to assist us in planning, executing, and experiencing the trip, we were able to elevate our vacation to another level. I hope that by sharing this, you’ll give yourself permission to leverage expertise for your next vacation.

I want to clarify upfront that I have no financial relationship with any of the companies or organizations I’m going to mention in this episode. I simply had a great experience, and I want to share that with you.

There are five different types of experts who supported our trip. The first one, and if you listen to nothing else in this episode, this alone will be worth it: We initially planned not to use any kind of vacation planner or support to organize this trip. In the last episode, I mentioned that when we traveled to Europe five years ago, my husband and I did all the planning ourselves. We figured out the plane tickets, where we wanted to go, where we wanted to stay, and what we wanted to see—all independently. It worked for us at that time. We had a successful trip, and it’s certainly one way to do it.

This year, however, we found ourselves under some time pressure, and we needed to get our act together quickly to orchestrate the trip. All I knew when I started planning was that Portugal was going to be the anchor—our number one destination. If possible, I wanted to see a bit of Spain, and if we could get to Morocco, that would be amazing. So, I Googled something like “planning a trip to Portugal for five people” or “planning a trip to Portugal with my family.” I was sitting on my patio when I came across a company called KimKim. Initially, I thought it might be an Asian company, but it’s actually a Silicon Valley-based company that pairs you with local travel experts who can help plan your trip.

On a whim, I filled out their survey, providing information about who was traveling with me, the ages of our travelers, and our interests—like food, special interests, or outdoor adventures. We also specified preferences for accommodations, transportation, and more. After submitting the survey, I was matched with a travel planner named Rita. She sent back an initial outline of an itinerary, including accommodations, excursions, and transportation. This was essentially a rough draft, but it was presented in a very compelling way.

Rita and I entered into a chat-based exchange to refine the itinerary. We went back and forth about six or seven times, and our final itinerary was version seven. It’s important to note that all of this initial planning and back-and-forth was completely free. The only time there was a cost was when we actually booked the trip. I was delighted by this, as I expected there would be an upfront fee, but there wasn’t.

What I loved about working with Rita, and I’ve checked this across different experiences, is that KimKim works with local planners worldwide. So, once you decide where you want to go, you’re matched with someone who has on-the-ground expertise in that country. For instance, Rita lives in Portugal and provided valuable context for our trip. I recommended KimKim to a friend traveling to China later this year, and her planner has expertise in China. This local expertise is invaluable.

As we continued working with Rita, she provided detailed itineraries that included photography, links to accommodations, and more. She did an excellent job reflecting our feedback. Eventually, we booked the trip through KimKim. For a one-time fee, we had everything except our international flights included. This allowed us to get a clear picture of our total investment in the trip, and Rita worked within our budget to make the necessary trade-offs.

For context, our international flights were from the U.S. to Madrid and then back from Morocco. Rita booked everything else—flights, train rides, private drivers, and accommodations. We stayed in various places, from a two-bedroom apartment in Madrid to a suite in Porto, and a traditional riad in Marrakech. The level of detail and care that Rita and her team provided was exceptional.

We also booked several excursions through KimKim, like a kayaking trip in the Algarve, which Rita connected us with. This brings me to another crucial type of expert: local guides and drivers. I cannot stress enough how having knowledgeable local guides made our trip better. For instance, when we landed in Marrakech, we were out of our element. Having a driver with our name on a sign was incredibly reassuring.

The third group of experts I want to mention are the hotel staff. As someone who studied hospitality, I have a deep appreciation for the art of hospitality. We had both good and not-so-good experiences on this trip, but there were several members of the hotel staff who were outstanding. One example is a young man named Mustafa in Marrakech, who met us at our car, helped with our luggage, and provided such warm and welcoming service that it left a lasting impression.

Overall, our experience with experts—whether it was Rita from KimKim, local guides, or exceptional hotel staff—made our vacation extraordinary. I hope you’ll consider leveraging expertise on your next trip to create a memorable and stress-free experience.